1-Naphthalenamine, hydrochloride (1:1) → HCID 178436389, compound

HRID 2371592Notes

Reaction equation

HRID 2371592 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1)[CH3:2].Cl.[C:13]1([NH2:23])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1>ClC1C=CC=CC=1>[C:13]1([NH:23][C:10]([NH:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[CH:4]=2)=[NH:11])[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 110941-Naphthalenamine, hydrochloride (1:1)HCID 10012043[(3-Ethylphenyl)amino]carbonitrile

Product 1

HCID 178436389HCID 178436389, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of m-ethylphenylcyanamide (730 mg, 2.99 mmol) and 1-naphthylamine hydrochloride (900 mg, 5.05 mmol) in chlorobenzene (20 ml) was heated at 140°-145° C. for 12 hours. It was allowed to cool to room temperature, concentrated and the residue was partitioned between dichloromethane and 10% NaOH solution. The organic layer was concentrated and the resulting residue was recrystallized from abs. EtOH-H2O to give N-(1-naphthyl)-N'-(m-ethylphenyl)guanidine (55 mg, 4%) as off-white needles. mp 96°-98° C.

Workup

  1. concentrationconcentrated
  2. customthe residue was partitioned between dichloromethane and 10% NaOH solution
  3. concentrationThe organic layer was concentrated
  4. customthe resulting residue was recrystallized from abs

Sources & evidence

ORD record
ord-c6d1cb65b1ad42258f2141a3454e0c4d
Source dataset
uspto-grants-1992_03
Patent number
US05093525

Reaction notes

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